Reactivities of vinyl azides and their recent applications in nitrogen heterocycle synthesis

Bao Hu, Stephen G. Dimagno

Research output: Contribution to journalArticlepeer-review

165 Scopus citations


Nitrogen heterocycles are abundant in natural products and pharmaceuticals. An emerging interest among synthetic chemists is to apply vinyl azides as a pivotal three-atom synthon for the construction of structurally complex and diverse N-heterocyclic skeletons. The unique features of the azide group connected to an alkene moiety permit vinyl azides to function as electrophiles, nucleophiles, or radical acceptors; their access to diverse reaction pathways provides great opportunities to generate highly reactive intermediates with often unusual or unconventional reactivities. This tutorial review will systematically illustrate the reactivities of vinyl azides and describe recent breakthroughs in the development of new transformations that create N-heterocycles.

Original languageEnglish (US)
Pages (from-to)3844-3855
Number of pages12
JournalOrganic and Biomolecular Chemistry
Issue number13
StatePublished - Apr 7 2015

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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